Tuscany by bike: Siena and val d'Orcia

Make your own way to Siena, one of Tuscany's most beautiful medieval cities.

Take the opportunity to explore its charming historic centre, wander through its narrow streets and discover the famous Piazza del Campo, home to the traditional Palio horse race.

Your first cycling stage takes you through the beautiful landscapes of the Chianti Senese, surrounded by vineyards, forests and rolling hills.

Along the way, discover Brolio Castle and the charming village of Villa a Sesta before reaching Asciano, on the edge of the Crete Senesi.

The scenery gradually changes as the vineyards give way to the distinctive clay hills that make this part of Tuscany so special.

Route: A mix of gentle climbs and descents, including approximately 13 km of well-maintained unpaved roads.

Approximately 49km.

Today's ride takes you through the remarkable landscapes of the Crete Senesi towards the famous Val d'Orcia.

Along the way, visit the impressive Monte Oliveto monastery complex, the medieval village of San Giovanni d'Asso and the monastery of Sant'Anna in Camprena.

The day ends in Pienza, a true Renaissance gem, renowned for its elegant architecture and spectacular views over the surrounding countryside.

Route: Approximately 12 km of unpaved tracks, followed by quiet paved roads with very little traffic.

Approximately 52km.

Continue exploring the beautiful Val d'Orcia, cycling past golden wheat fields, cypress-lined roads and the rolling hills that have made Tuscany famous.

Pass through the historic centre of San Quirico d'Orcia before reaching Montalcino, famous for its prestigious Brunello wine.

The route then continues towards Buonconvento and the Val d'Arbia, ending in the small medieval village of Murlo.

Route: Approximately 15 km of unpaved roads, with the remaining distance on paved roads.

Approximately 56 km.

Today's stage leads you through the rolling landscapes of the Montagnola Senese and Val d'Elsa, following sections of the historic Via Francigena, an ancient pilgrimage route connecting Northern Europe to Rome.

One of the highlights is Monteriggioni, a remarkable fortified medieval village surrounded by its impressive defensive walls.

The day ends in Colle Val d'Elsa, where the historic centre retains all the charm and character of a traditional Tuscan town.

Route: A combination of quiet paved roads and unpaved country tracks.

Distance: approximately 64km.

Enjoy a beautiful ride through the Tuscan countryside, with wonderful panoramic views stretching across Val di Cecina and Val d'Elsa.

Cycle through Casole d'Elsa before continuing towards Volterra, an ancient Etruscan town perched high on a hill.

The final uphill kilometres bring you to this fascinating historic town, known for its medieval streets, impressive monuments and authentic atmosphere.

Route: Mainly paved roads, with a climb over the final kilometres to reach Volterra.

Approximately 47km.

On your final cycling day, ride through the beautiful hills of the Valdera towards one of Tuscany's most famous towns: San Gimignano, renowned for its distinctive medieval towers.

After exploring its charming historic centre, continue to Certaldo, the birthplace of the writer Boccaccio, whose picturesque old town is also well worth a visit.

From Certaldo, take the train back to Siena for your final night.

Route: Entirely on paved roads. Return to Siena by train from Certaldo.

Approximately 47 km

Enjoy breakfast at your accommodation before your trip comes to an end.

Leave Tuscany with wonderful memories of its historic villages, rolling landscapes, beautiful vineyards and delicious local flavours.

Had an amazing time on our short, self-guided bike trip through Tuscany. The area is beautiful, especially the stretch from the outskirts of Florence to Radda in Chianti. Lots of wineries with consistently good wine. Everything was well coordinated in terms of bike delivery, luggage transport, and hotel booking. Had some initial difficulty with the bikes and with navigation but everything went smoothly afterwards.